(cis,trans)-2,3-dihydro-2,3-dimethyl-9-hydroxy-8-propyl-4H,6H-benzo<1,2-b:3,4-b>dipyran-4,6-dione | 185824-43-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (cis,trans)-2,3-dihydro-2,3-dimethyl-9-hydroxy-8-propyl-4H,6H-benzo<1,2-b:3,4-b>dipyran-4,6-dione
• 英文别名: 5-Hydroxy-8,9-dimethyl-4-propyl-9,10-dihydro-2H,8H-pyrano[2,2-f]chromene-2,10-dione；5-hydroxy-8,9-dimethyl-4-propyl-8,9-dihydropyrano[2,3-f]chromene-2,10-dione；5-hydroxy-8,9-dimethyl-4-propyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione；5-hydroxy-8,9-dimethyl-4-propyl-8,9-dihydropyrano[2,3-h]chromene-2,10-dione
• CAS: 185824-43-5
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: NEXQWEILTXDXHO-UHFFFAOYSA-N

物化性质

• 沸点：
  521.9±50.0 °C(predicted)
• 密度：
  1.249±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (cis,trans)-2,3-dihydro-2,3-dimethyl-9-hydroxy-8-propyl-4H,6H-benzo<1,2-b:3,4-b>dipyran-4,6-dione 在 sodium tetrahydroborate 、 cerium(III) chloride 、 四丁基碘化铵 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 82.0h， 生成 (10S,11R,12R)-12-羟基-6,6,10,11-四甲基-4-丙基-11,12-二氢-2H,6H,10H-二吡喃并[2,3-f:2',3'-h]色烯-2-酮
  参考文献：
  名称：

  Total synthesis of (.+-.)-calanolide A, a non-nucleoside inhibitor of HIV-1 reverse transcriptase

  摘要：

  The first syntheses of (+/-)-calanolide A and the related (+/-)-calanolides C and D have been carried out in a short sequence using a Lewis acid-promoted Claisen rearrangement to establish the chromene ring.

  DOI：

  10.1021/jo00073a015
• 作为产物：
  描述：

  5,7-dihydroxy-8-(2-methyl-2-buten-1-onyl)-4-propyl-2H-1-benzopyran-2-one 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 2.0h， 以89%的产率得到(cis,trans)-2,3-dihydro-2,3-dimethyl-9-hydroxy-8-propyl-4H,6H-benzo<1,2-b:3,4-b>dipyran-4,6-dione
  参考文献：
  名称：

  Total synthesis of (.+-.)-calanolide A, a non-nucleoside inhibitor of HIV-1 reverse transcriptase

  摘要：

  The first syntheses of (+/-)-calanolide A and the related (+/-)-calanolides C and D have been carried out in a short sequence using a Lewis acid-promoted Claisen rearrangement to establish the chromene ring.

  DOI：

  10.1021/jo00073a015

文献信息

• Ytterbium Triflate Mediated Selective Deprotection of Acetates
  作者：G. V. M. Sharma、A. Ilangovan

  DOI：10.1055/s-1999-2975

  日期：1999.12

  Ytterbium triflate mediated selective deprotection of acetates in isopropyl alcohol at reflux temperature is reported. Unlike hafnium triflate, under the present reaction conditions aryl acetates also undergo deacetylation instead of Fries migration.

  报道了一种在回流温度下以异丙醇作为溶剂，利用三氟化镱作为催化剂进行乙酸酯类化合物选择性脱保护的方法。与三氟化铪不同，在本反应条件下，芳基乙酸酯同样会发生脱乙酰反应而非弗里斯重排。
• Pyranocoumarin compounds as a novel pharmacophore with anti-TB activity
  申请人：——

  公开号：US20030083369A1

  公开（公告）日：2003-05-01

  The present invention relates to compounds and compositions useful in treating or preventing conditions and diseases related to Mycobacterium infection, and methods of use directed thereto.

  本发明涉及用于治疗或预防与分枝杆菌感染相关的疾病和状况的化合物和组合物，以及相应的使用方法。
• A Mild and Highly Selective Deprotective Method of Prenyl Ethers Using Ytterbium Triflate
  作者：G. V. M. Sharma、A. Ilangovan、A. K. Mahalingam

  DOI：10.1021/jo9804846

  日期：1998.11.1
• Pyranocoumarin, a novel anti-TB pharmacophore: Synthesis and biological evaluation against Mycobacterium tuberculosis
  作者：Ze-Qi Xu、Krzysztof Pupek、William J. Suling、Livia Enache、Michael T. Flavin

  DOI：10.1016/j.bmc.2006.02.017

  日期：2006.7

  Pyranocoumarin compounds were identified to embody a novel and unique pharmacophore for anti-TB activity. A systematic approach was taken to investigate the structural characteristics. Focused libraries of compounds were synthesized and evaluated for their anti-TB activity in primary screening assays. Compounds shown to be active were further determined for MIC and MBC values. Three of the four bactericidal compounds (16, 17c, and 18f) were amino derivatives, with MIC values of 16 mu g/mL and respective MBC values of 32, 32, and 64 mu g/mL. (c) 2006 Elsevier Ltd. All rights reserved.
• PYRANOCOUMARIN COMPOUNDS AS A NOVEL PHARMACOPHORE WITH ANTI-TB ACTIVITY
  申请人：Sarawak Medichem Pharmaceuticals, Inc.

  公开号：EP1379529A2

  公开（公告）日：2004-01-14